[A simple method of synthesis of S-sulfoxides of penicillanic acid and 6-alpha-bromo[chloro]-penicillanic acids]

Antibiot Khimioter. 1990 Aug;35(8):12-3.
[Article in Russian]

Abstract

A simple method for synthesis of S-sulfoxides of penicillanic acid and 6 alpha-bromo- and 6 alpha-chloropenicillanic acids is described. The S-sulfoxides were synthesized by the respective oxidation with 30% hydrogen peroxide at 0 degrees C in the absence of solvents. 1 mol of penicillanic acid and 1.5 to 2 mol of 6 alpha-bromo- or 6 alpha-chloropenicillanic acid were required. The yields of S-sulfoxides of 6 alpha-bromo- and 6 alpha-chloropenicillanic acids amounted to 55 and 50%, respectively, based on 6-aminopenicillanic acid. The yield of penicillanic acid S-sulfoxide was 80% based on penicillanic acid. The purity of the compounds was more than 95%.

Publication types

  • English Abstract

MeSH terms

  • Hydrogen Peroxide / pharmacology*
  • Penicillanic Acid / chemical synthesis*
  • Penicillanic Acid / chemistry
  • Spectrophotometry, Infrared / methods
  • Sulfoxides / chemical synthesis*
  • Sulfoxides / chemistry
  • beta-Lactamase Inhibitors*

Substances

  • Sulfoxides
  • beta-Lactamase Inhibitors
  • brobactam
  • 6-bromopenicillanic acid S-sulfoxide
  • Penicillanic Acid
  • 6-chloropenicillanic acid S-sulfoxide
  • Hydrogen Peroxide